91890-00-5

Basic information

• Product Name: (Z)-2-Buten-2-ylboronic acid pinacol ester
• Synonyms: 1,3,2-Dioxaborolane, 4,4,5,5-tetramethyl-2-[(1Z)-1-methyl-1-propen-1-yl]-;(Z)-2-Buten-2-ylboronic acid pinacol ester
• CAS NO: 91890-00-5
• Molecular Formula: C₁₀H₁₉BO₂
• Molecular Weight: 200.08294
• Mol File: 91890-00-5.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (Z)-2-Buten-2-ylboronic acid pinacol ester(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-2-Buten-2-ylboronic acid pinacol ester(91890-00-5)
• EPA Substance Registry System: (Z)-2-Buten-2-ylboronic acid pinacol ester(91890-00-5)

Safety Data

• Hazardous Substances Data: 91890-00-5(Hazardous Substances Data)

Usage

General Description

(Z)-2-Buten-2-ylboronic acid pinacol ester is a chemical compound with the molecular formula C10H19BO2. It is commonly used as a reagent in organic synthesis due to its ability to form carbon-carbon bonds through cross-coupling reactions, particularly in the Suzuki-Miyaura reaction. (Z)-2-Buten-2-ylboronic acid pinacol ester is typically used in the formation of complex organic molecules, such as pharmaceuticals and agrochemicals, and is known for its stability and ease of handling. Its pinacol ester group provides additional stability and solubility in organic solvents, making it a versatile tool for synthetic chemists in the development of new materials and chemical products. Additionally, its use in the formation of carbon-carbon bonds makes it a crucial building block in the construction of diverse chemical structures.

Upstream product

• 177949-90-5 4,4,5,5-tetramethyl-2-(oct-1-en-2-yl)-1,3,2-dioxaborolane 
• 75851-67-1 4,4,5,5-tetramethyl-2-(1-methyl-2-propenyl)-1,3,2-dioxaborolane 
• 503-17-3 dimethylacetylene 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 

Downstream Products

• 1622201-99-3 (2S,3E)-3-methyl-2-phenyl-2-(4',4',5',5'-tetramethyl-1’,3’,2’-dioxaborolanyl)pent-3-ene 
• 1622202-01-0 (2E,4S)-3-methyl-4-phenyl-4-(4',4',5',5'-tetramethyl-1’,3’,2’-dioxaborolanyl)hex-2-ene 

Relevant articles and documents

Pincer Iron Hydride Complexes for Alkene Isomerization: Catalytic Approach to Trisubstituted (Z)-Alkenyl Boronates

An iron dichloride complex [Fe]Cl2 supported by a pincer phosphine-pyridine-imidazoline (PNNimid) ligand {[Fe]Cl2 = (PNNimid)FeCl2}, upon activation with NaHBEt3, catalyzes the isomerization of 1,1-disubstituted alkenyl boronates to synthetically valuable

Tris(2,4,6-trifluorophenyl)borane: An Efficient Hydroboration Catalyst

The metal-free catalyst tris(2,4,6-trifluorophenyl)borane has demonstrated its extensive applications in the 1,2-hydroboration of numerous unsaturated reagents, namely alkynes, aldehydes and imines, consisting of a wide array of electron-withdrawing and donating functionalities. A range of over 50 borylated products are reported, with many reactions proceeding with low catalyst loading under ambient conditions. These pinacol boronate esters, in the case of aldehydes and imines, can be readily hydrolyzed to leave the respective alcohol and amine, whereas alkynyl substrates result in vinyl boranes. This is of great synthetic use to the organic chemist.